Sail the USVI: Snorkel, Beach Bars & Private Charters from Saint John
Full-day sails and private charters departing Saint John's — island beaches, reef snorkeling, and customizable itineraries on Calypso Charters.
Featured Tours & Private Charters
Choose from day sails to Jost Van Dyke, LimeOut excursions, or private trips aboard CAT 5.
About Calypso Charters
Calypso Charters is a Saint John–based boat operator offering day sails and private charters in the U.S. and British Virgin Islands. Operating from Saint John's, Saint John, Calypso Charters runs three signature experiences: the Calypso - Jost Van Dyke Sail (an 8-hour sailing adventure), A Trip to LimeOut (a 7-hour day trip), and the CAT 5 private charter aboard a 36’ power catamaran with capacity for up to 12 guests.
Each full-day trip includes on-board amenities described in the trip summaries: continental breakfast and an open bar are provided on select departures, snorkeling stops at prime reef locations, and beach time at White Bay and other St. John beaches. The Jost Van Dyke sail features breakfast, snorkeling, Great Harbor exploration, and time in White Bay. The LimeOut trip focuses on remote barrier island snorkeling, tacos and craft cocktails at LimeOut, and beach access. The CAT 5 private charter offers a customizable itinerary, sunbathing on bean bag chairs, and a smooth ride for small groups.
Calypso Charters emphasizes personalized private charters and small-group day trips. Guests booking the CAT 5 can expect a maximum of 12 passengers, enabling an intimate experience and flexible route planning. Departure point is Saint John's, Saint John, providing convenient access for visitors to St. John and nearby islands. Trip durations are listed per experience, with the Calypso - Jost Van Dyke Sail running approximately eight hours and A Trip to LimeOut about seven hours; private CAT 5 charters are scheduled based on customer selection. Detailed itineraries, on-board inclusions, and vessel information are provided on the listing to help travelers make an informed booking decision on The Adventure Collective.
Book a Day Sail or Private Charter from Saint John
Reserve the Calypso - Jost Van Dyke Sail, A Trip to LimeOut, or the CAT 5 private charter today — clear itineraries and vessel details make booking simple.